University Chemistry ›› 2023, Vol. 38 ›› Issue (10): 250-257.doi: 10.3866/PKU.DXHX202212063

• Chemistry Laboratory • Previous Articles     Next Articles

Synthesis of Diethyl 2-Benzyl-3, 4-dioxo-6-phenyl-9-vinyl-2-azaspiro [4.4]nonane-7, 7-dicarboxylate through Palladium Catalyzed Tandem Cyclization: Introducing a Comprehensive Experiment of Organic Chemistry

Yicheng Luo1, Yanfeng Gao1, Weisheng Lin2, Zhiwei Miao1,*()   

  1. 1 State Key Laboratory of Elemento-Organic Chemistry, College of Chemistry, Nankai University, Tianjin 300071, China
    2 Department of Ecological and Resources Engineering, Wuyi University, Wuyishan 354300, Fujian Province, China
  • Received:2022-12-23 Accepted:2023-03-07 Published:2023-03-22
  • Contact: Zhiwei Miao E-mail:miaozhiwei@nankai.edu.cn

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Abstract:

The comprehensive experiment of organic chemistry is conducive to training students' experimental skills, cultivating their innovative ability, and stimulating their independent thinking ability and research consciousness. This article presents a comprehensive organic chemistry experiment in which 2-vinylcyclopropane-1, 1-diethyl diformate and 1-benzyl-4-benzylidene-2, 3-pyrrolidone were used as reactants to synthesize 2-benzyl-3, 4-dicarbonyl-6-phenyl-9-vinyl-2-azanone-7, 7-dicarboxylate ethyl ester by palladium-catalyzed tandem cyclization reaction. 1H NMR, 13C NMR and HRMS characterized the structure of the product.

Key words: Organic chemistry comprehensive experiment, Palladium catalysis, Tandem cyclization reaction, Diethyl 2-benzyl-3, 4-dioxo-6-phenyl-9-vinyl-2-azaspiro[4.4]nonane-7, 7-dicarboxylate, Synthesis and structural characterization